Trimethyl borate → HCID 18795258, compound

HRID 1003131Notes

Reaction equation

HRID 1003131 reaction equation
C([Li])CCC.[CH2:6]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[B:26](OC)([O:29]C)[O:27]C>C1COCC1>[CH2:6]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([B:26]([OH:29])[OH:27])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 3126212HCID 3126212, compoundHCID 178418339Butyllithium

Product 1

HCID 18795258HCID 18795258, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

9 ml of n-butyl lithium (1.68M hexane solution) was added dropwise to a solution of 5 g of 5-heptyl-2-(4-bromophenyl) pyridine prepared by the method described in Toku-Kai-Sho 60-163864 in 100 ml of THF with maintaining at -60° C. After stirring for 30 minutes with maintaining at -60° C., 3 g of trimethyl borate was added and stirred for further 1 hour. After the inner temperature was recovered gradually to the room temperature, 40 ml of 6N hydrochloric acid was added and then THF was distilled off. The formed solid was filtered and recrystallized, to obtain 3 g of 4-(5-heptylpyridin-2-yl)phenyl boronic acid. Melting point; 206-214° C.

Workup

  1. customprepared by the method
  2. temperaturewith maintaining at -60° C.
  3. stirringstirred for further 1 hour
  4. customAfter the inner temperature was recovered gradually to the room temperature, 40 ml of 6N hydrochloric acid
  5. additionwas added
  6. distillationTHF was distilled off
  7. filtrationThe formed solid was filtered
  8. customrecrystallized

Sources & evidence

ORD record
ord-eed2201243ee45c08b6d7f059aa3e6d0
Source dataset
uspto-grants-2000_04
Patent number
US06045720

Reaction notes

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